Airbnb Properties for Sale in Winter Park, FL

Looking for a vacation rental investment in Winter Park, FL with high ROI ?

Explore a range of newly added short-term rental homes in Winter Park, FL. Make a smart investment with newly available Airbnb properties and find the ideal high-ROI property for sale.

Airbnb Condo For Sale in Winter Park, FL

Search for Condo for Sale in Winter Park, Florida. Browse all of Mashvisor’s Condo listings and other investment property types including Single Family Homes, Multi Family Homes, Condos, Townhouses and Other Homes.

Showing 61 Condo listings of over 500,000 total investment properties for sale. Visit Mashvisor.com to all investment properties.

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PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
150 Killarney Bay Ct #5 Winter Park, FL Tucked away in the hidden gem of Killarney Bay, this move-in ready condo offers the perfec...	2 beds \| 2 baths \| 1,140 sq.ft.	$325,000	Airbnb cash on cash: 4.65% Traditional cash on cash: 3.69% Airbnb Rental Income: $3260 Traditional Rental Income: $2233 Airbnb ROI: 4.65% Traditional ROI: 3.69%
2500 Lee Rd #232 Winter Park, FL Enjoy carefree living in this lovely community located on beautiful Lake Killarney. A com...	1 beds \| 1 baths \| 645 sq.ft.	$164,900	Airbnb cash on cash: 7.2% Traditional cash on cash: 5.18% Airbnb Rental Income: $2412 Traditional Rental Income: $1504 Airbnb ROI: 7.2% Traditional ROI: 5.18%
311 E Morse Blvd #7-19 Winter Park, FL 55+.Studio at a great price! This condominium is in Winter Parkâs established Whispering...	1 beds \| 1 baths \| 482 sq.ft.	$289,900	Airbnb cash on cash: 1.08% Traditional cash on cash: -0.31% Airbnb Rental Income: $2412 Traditional Rental Income: $1443 Airbnb ROI: 1.08% Traditional ROI: -0.31%
2500 Lee Rd #208 Winter Park, FL This charming two-bedroom, two-bathroom 2nd floor condo offers the perfect blend of comfor...	2 beds \| 2 baths \| 956 sq.ft.	$180,000	Airbnb cash on cash: 9.58% Traditional cash on cash: 7.87% Airbnb Rental Income: $3260 Traditional Rental Income: $2235 Airbnb ROI: 9.58% Traditional ROI: 7.87%
184 Sandlewood Trl #2 Winter Park, FL FHA, VA, and DPA approved. Nestled just minutes from the charming boutiques and award-winn...	2 beds \| 2 baths \| 1,133 sq.ft.	$314,000	Airbnb cash on cash: 5.16% Traditional cash on cash: 3.7% Airbnb Rental Income: $3260 Traditional Rental Income: $2099 Airbnb ROI: 5.16% Traditional ROI: 3.7%
311 E Morse Blvd #7-5 Winter Park, FL Major Price Improvement! Here is your rare opportunity to own a studio apartment in Whispe...	1 beds \| 1 baths \| 482 sq.ft.	$359,000	Airbnb cash on cash: 0.54% Traditional cash on cash: 0.12% Airbnb Rental Income: $2412 Traditional Rental Income: $1680 Airbnb ROI: 0.54% Traditional ROI: 0.12%
151 N Orlando Ave #115 Winter Park, FL Welcome to Lake Killarney Living ... Where Winter Park charm meets everyday convenience. F...	2 beds \| 1 baths \| 710 sq.ft.	$298,000	Airbnb cash on cash: 4.78% Traditional cash on cash: 3.16% Airbnb Rental Income: $3260 Traditional Rental Income: $2075 Airbnb ROI: 4.78% Traditional ROI: 3.16%
2500 Lee Rd #222 Winter Park, FL Lakefront access in Winter Park under $200K! One of the few condos at this price point off...	1 beds \| 1 baths \| 645 sq.ft.	$189,500	Airbnb cash on cash: 6.59% Traditional cash on cash: 6.4% Airbnb Rental Income: $2412 Traditional Rental Income: $1787 Airbnb ROI: 6.59% Traditional ROI: 6.4%
1809 Hammerlin Ave Winter Park, FL 1809 Hammerlin Ave, Winter Park, FL 32789 \| Condo/Coop	3 beds \| 2 baths \| 1,818 sq.ft.	$549,000	Airbnb cash on cash: 3.75% Traditional cash on cash: 2.17% Airbnb Rental Income: $4337 Traditional Rental Income: $2615 Airbnb ROI: 3.75% Traditional ROI: 2.17%
2500 Lee Rd #237 Winter Park, FL 2500 Lee Rd #237, Winter Park, FL 32789 \| Condo/Coop	1 beds \| 1 baths \| 645 sq.ft.	$169,000	Airbnb cash on cash: 7.19% Traditional cash on cash: 2.96% Airbnb Rental Income: $2412 Traditional Rental Income: $1140 Airbnb ROI: 7.19% Traditional ROI: 2.96%
1500 Gay Rd #24B Winter Park, FL 1500 Gay Rd #24B, Winter Park, FL 32789 \| Condo/Coop	2 beds \| 2 baths \| 1,026 sq.ft.	$261,500	Airbnb cash on cash: 6.07% Traditional cash on cash: 2.54% Airbnb Rental Income: $3260 Traditional Rental Income: $1657 Airbnb ROI: 6.07% Traditional ROI: 2.54%
311 E Morse Blvd #7-11 Winter Park, FL 311 E Morse Blvd #7-11, Winter Park, FL 32789 \| Condo/Coop	1 beds \| 1 baths \| 570 sq.ft.	$309,900	Airbnb cash on cash: 0.85% Traditional cash on cash: -1.6% Airbnb Rental Income: $2412 Traditional Rental Income: $1107 Airbnb ROI: 0.85% Traditional ROI: -1.6%
2500 Lee Rd #202 Winter Park, FL 2500 Lee Rd #202, Winter Park, FL 32789 \| Condo/Coop	2 beds \| 2 baths \| 956 sq.ft.	$224,999	Airbnb cash on cash: 7.3% Traditional cash on cash: 2.66% Airbnb Rental Income: $3260 Traditional Rental Income: $1540 Airbnb ROI: 7.3% Traditional ROI: 2.66%
630 Killarney Bay Ct #3 Winter Park, FL Lakefront townhome in desirable Killarney Bay directly on Lake Killarney, offering 2 bedro...	2 beds \| 2 baths \| 1,428 sq.ft.	$495,000	Airbnb cash on cash: 1.87% Traditional cash on cash: 1.84% Airbnb Rental Income: $3260 Traditional Rental Income: $2514 Airbnb ROI: 1.87% Traditional ROI: 1.84%
1500 Gay Rd #5 Winter Park, FL 1500 Gay Rd #5, Winter Park, FL 32789 \| Condo/Coop	1 beds \| 1 baths \| 732 sq.ft.	$170,000	Airbnb cash on cash: 6.6% Traditional cash on cash: 2.1% Airbnb Rental Income: $2412 Traditional Rental Income: $1091 Airbnb ROI: 6.6% Traditional ROI: 2.1%
1500 Gay Rd #20D Winter Park, FL 1500 Gay Rd #20D, Winter Park, FL 32789 \| Condo/Coop	2 beds \| 2 baths \| 1,026 sq.ft.	$262,000	Airbnb cash on cash: 6.06% Traditional cash on cash: 1.45% Airbnb Rental Income: $3260 Traditional Rental Income: $1388 Airbnb ROI: 6.06% Traditional ROI: 1.45%
1807 Hammerlin Ave #G Winter Park, FL Price Improvement Welcome home to this beautifully updated two-story end-unit, ideally...	3 beds \| 2 baths \| 1,818 sq.ft.	$550,000	Airbnb cash on cash: 3.5% Traditional cash on cash: 2.58% Airbnb Rental Income: $4337 Traditional Rental Income: $2954 Airbnb ROI: 3.5% Traditional ROI: 2.58%
851 MILES AVENUE #13 Winter Park, FL Under contract-accepting backup offers. Welcome to 851 Miles Ave #13, a beautifully renova...	2 beds \| 1 baths \| 808 sq.ft.	$209,999	Airbnb cash on cash: 7.99% Traditional cash on cash: 5.31% Airbnb Rental Income: $3260 Traditional Rental Income: $1995 Airbnb ROI: 7.99% Traditional ROI: 5.31%
1000 S Semoran Blvd #715 Winter Park, FL Prime location meets exceptional value in the highly sought-after Winter Park area! This f...	1 beds \| 1 baths \| 735 sq.ft.	$122,990	Airbnb cash on cash: 8.99% Traditional cash on cash: 7.59% Airbnb Rental Income: $2412 Traditional Rental Income: $1655 Airbnb ROI: 8.99% Traditional ROI: 7.59%
2918 Antique Oaks Cir #25 Winter Park, FL 2 Bedroom 2 bath condo 1 block south of University Blvd great location for UCF or Full Sai...	2 beds \| 2 baths \| 1,018 sq.ft.	$189,000	Airbnb cash on cash: 8.74% Traditional cash on cash: 5.41% Airbnb Rental Income: $3260 Traditional Rental Income: $1930 Airbnb ROI: 8.74% Traditional ROI: 5.41%
7336 Forest Hill Ct #240 Winter Park, FL Updated Winter Park Townhome!! If you are looking for LOCATION this is the property for yo...	2 beds \| 1 baths \| 990 sq.ft.	$169,900	Airbnb cash on cash: 9.27% Traditional cash on cash: 6.19% Airbnb Rental Income: $3260 Traditional Rental Income: $2029 Airbnb ROI: 9.27% Traditional ROI: 6.19%
144 Lewfield Cir #144 Winter Park, FL LOCATION! LOCATION! LOCATION! Beautiful 2nd floor corner condo in desirable Winter Park, f...	1 beds \| 1 baths \| 678 sq.ft.	$137,000	Airbnb cash on cash: 8.66% Traditional cash on cash: 6.84% Airbnb Rental Income: $2412 Traditional Rental Income: $1582 Airbnb ROI: 8.66% Traditional ROI: 6.84%
7484 Canford Ct #8 Winter Park, FL This three-bedroom, three-bath updated Winter Park townhome-style condo is located in a qu...	3 beds \| 2 baths \| 1,578 sq.ft.	$250,000	Airbnb cash on cash: 9.92% Traditional cash on cash: 4.89% Airbnb Rental Income: $4337 Traditional Rental Income: $2239 Airbnb ROI: 9.92% Traditional ROI: 4.89%
189 Lewfield Cir #189 Winter Park, FL Experience the best of the Winter Park lifestyle in this beautifully updated first-floor c...	1 beds \| 1 baths \| 678 sq.ft.	$155,000	Airbnb cash on cash: 6.87% Traditional cash on cash: 5.43% Airbnb Rental Income: $2412 Traditional Rental Income: $1609 Airbnb ROI: 6.87% Traditional ROI: 5.43%
4772 Tangerine Ave #4772 Winter Park, FL perfect starter home to fix up. Needs some rehab work to build to your perfect home. has...	2 beds \| 2 baths \| 1,058 sq.ft.	$199,000	Airbnb cash on cash: 8.84% Traditional cash on cash: 3.3% Airbnb Rental Income: $3260 Traditional Rental Income: $1483 Airbnb ROI: 8.84% Traditional ROI: 3.3%
2923 Antique Oaks Cir #37 Winter Park, FL Don't miss this opportunity to own a ground floor, end unit condo in an amazing location! ...	2 beds \| 2 baths \| 1,105 sq.ft.	$196,400	Airbnb cash on cash: 8.66% Traditional cash on cash: 5.52% Airbnb Rental Income: $3260 Traditional Rental Income: $1943 Airbnb ROI: 8.66% Traditional ROI: 5.52%
3019 Antique Oaks Cir #124 Winter Park, FL READY TO BE SOLD! Accepting great offers. Welcome home! NEWLY RENOVATED BATHROOM on deck. ...	1 beds \| 1 baths \| 749 sq.ft.	$149,000	Airbnb cash on cash: 7.44% Traditional cash on cash: 6.99% Airbnb Rental Income: $2412 Traditional Rental Income: $1758 Airbnb ROI: 7.44% Traditional ROI: 6.99%
4768 Tangerine Ave #4768 Winter Park, FL Under contract-accepting backup offers. Seller Motivated! Clean and charming, this one-sto...	1 beds \| 1 baths \| 753 sq.ft.	$185,000	Airbnb cash on cash: 6.32% Traditional cash on cash: 4.72% Airbnb Rental Income: $2412 Traditional Rental Income: $1539 Airbnb ROI: 6.32% Traditional ROI: 4.72%
2383 Sun Valley Cir #2383 Winter Park, FL Nestled in a peaceful setting within the serene Cedarwood Village community, this charming...	2 beds \| 2 baths \| 1,295 sq.ft.	$269,000	Airbnb cash on cash: 5.47% Traditional cash on cash: 2.79% Airbnb Rental Income: $3260 Traditional Rental Income: $1847 Airbnb ROI: 5.47% Traditional ROI: 2.79%
126 Scottsdale Sq #126 Winter Park, FL Excellent opportunity to own this second-floor, 2-bedroom, 1/1-bath condo in a Convenientl...	2 beds \| 1 baths \| 1,085 sq.ft.	$150,000	Airbnb cash on cash: 7.52% Traditional cash on cash: 3.34% Airbnb Rental Income: $3260 Traditional Rental Income: $1928 Airbnb ROI: 7.52% Traditional ROI: 3.34%
296 LEWFIELD CIRCLE Winter Park, FL 1 bed, 1 bath condo in Winter Park	1 beds \| 1 baths \| 678 sq.ft.	$154,000	Airbnb cash on cash: 7.47% Traditional cash on cash: 5.72% Airbnb Rental Income: $2412 Traditional Rental Income: $1563 Airbnb ROI: 7.47% Traditional ROI: 5.72%
225 Lewfield Cir #225 Winter Park, FL One or more photo(s) has been virtually staged. **This property qualifies for a closing co...	2 beds \| 2 baths \| 953 sq.ft.	$220,000	Airbnb cash on cash: 7.74% Traditional cash on cash: 4.5% Airbnb Rental Income: $3260 Traditional Rental Income: $1852 Airbnb ROI: 7.74% Traditional ROI: 4.5%
7707 Country Pl #4 Winter Park, FL Beautifully updated 2BD/2BA single-story condo in peaceful Goldenrod Villas, Winter Park. ...	2 beds \| 2 baths \| 1,068 sq.ft.	$250,000	Airbnb cash on cash: 7.24% Traditional cash on cash: 4.58% Airbnb Rental Income: $3260 Traditional Rental Income: $1900 Airbnb ROI: 7.24% Traditional ROI: 4.58%
205 Lewfield Cir #205 Winter Park, FL Wonderful! Exceptional Winter Park location! Amenities include 2 pools, lighted tennis cou...	2 beds \| 2 baths \| 927 sq.ft.	$235,000	Airbnb cash on cash: 7.33% Traditional cash on cash: 3.77% Airbnb Rental Income: $3260 Traditional Rental Income: $1737 Airbnb ROI: 7.33% Traditional ROI: 3.77%
7468 Canford Ct #24 Winter Park, FL This charming 2-bedroom, 1.5-bath condo offers a desirable townhome-style layout with spac...	2 beds \| 1 baths \| 1,365 sq.ft.	$189,999	Airbnb cash on cash: 8.35% Traditional cash on cash: 6.64% Airbnb Rental Income: $3260 Traditional Rental Income: $2220 Airbnb ROI: 8.35% Traditional ROI: 6.64%
7471 Canford Ct #19 Winter Park, FL 7471 Canford Ct #19, Winter Park, FL 32792 \| Condo/Coop	2 beds \| 1 baths \| 1,393 sq.ft.	$199,000	Airbnb cash on cash: 7.62% Traditional cash on cash: 3.59% Airbnb Rental Income: $3260 Traditional Rental Income: $1765 Airbnb ROI: 7.62% Traditional ROI: 3.59%
3071 George Mason Ave #5 Winter Park, FL 3071 George Mason Ave #5, Winter Park, FL 32792 \| Condo/Coop	N/A beds \| 1 baths \| 549 sq.ft.	$89,900	Airbnb cash on cash: 9.13% Traditional cash on cash: 1.01% Airbnb Rental Income: $2207 Traditional Rental Income: $937 Airbnb ROI: 9.13% Traditional ROI: 1.01%
2923 Antique Oaks Cir #39 Winter Park, FL 2923 Antique Oaks Cir #39, Winter Park, FL 32792 \| Condo/Coop	2 beds \| 2 baths \| 1,105 sq.ft.	$184,999	Airbnb cash on cash: 9.17% Traditional cash on cash: 4.84% Airbnb Rental Income: $3260 Traditional Rental Income: $1767 Airbnb ROI: 9.17% Traditional ROI: 4.84%
3038 Antique Oaks Cir #166 Winter Park, FL 3038 Antique Oaks Cir #166, Winter Park, FL 32792 \| Condo/Coop	2 beds \| 2 baths \| 1,018 sq.ft.	$205,000	Airbnb cash on cash: 8.24% Traditional cash on cash: 3.89% Airbnb Rental Income: $3260 Traditional Rental Income: $1682 Airbnb ROI: 8.24% Traditional ROI: 3.89%
2384 Sun Valley Cir Winter Park, FL Great opportunity to own this 3 bedrooms, 2 bathrooms single-story, ground level, end unit...	3 beds \| 2 baths \| 1,311 sq.ft.	$269,900	Airbnb cash on cash: 9.66% Traditional cash on cash: 4.51% Airbnb Rental Income: $4337 Traditional Rental Income: $2116 Airbnb ROI: 9.66% Traditional ROI: 4.51%

Your search for investment property begins and ends here

Airbnb Condo For Sale in Winter Park, FL

150 Killarney Bay Ct #5

Winter Park, FL

2 beds | 2 baths | 1,140 sq.ft.

$325,000

Airbnb cash on cash: 4.65%

Traditional cash on cash: 3.69%

Airbnb Rental Income: $3260

Traditional Rental Income: $2233

Airbnb ROI: 4.65%

Traditional ROI: 3.69%

2500 Lee Rd #232

Winter Park, FL

1 beds | 1 baths | 645 sq.ft.

$164,900

Airbnb cash on cash: 7.2%

Traditional cash on cash: 5.18%

Airbnb Rental Income: $2412

Traditional Rental Income: $1504

Airbnb ROI: 7.2%

Traditional ROI: 5.18%

311 E Morse Blvd #7-19

Winter Park, FL

1 beds | 1 baths | 482 sq.ft.

$289,900

Airbnb cash on cash: 1.08%

Traditional cash on cash: -0.31%

Airbnb Rental Income: $2412

Traditional Rental Income: $1443

Airbnb ROI: 1.08%

Traditional ROI: -0.31%

2500 Lee Rd #208

Winter Park, FL

2 beds | 2 baths | 956 sq.ft.

$180,000

Airbnb cash on cash: 9.58%

Traditional cash on cash: 7.87%

Airbnb Rental Income: $3260

Traditional Rental Income: $2235

Airbnb ROI: 9.58%

Traditional ROI: 7.87%

184 Sandlewood Trl #2

Winter Park, FL

2 beds | 2 baths | 1,133 sq.ft.

$314,000

Airbnb cash on cash: 5.16%

Traditional cash on cash: 3.7%

Airbnb Rental Income: $3260

Traditional Rental Income: $2099

Airbnb ROI: 5.16%

Traditional ROI: 3.7%

311 E Morse Blvd #7-5

Winter Park, FL

1 beds | 1 baths | 482 sq.ft.

$359,000

Airbnb cash on cash: 0.54%

Traditional cash on cash: 0.12%

Airbnb Rental Income: $2412

Traditional Rental Income: $1680

Airbnb ROI: 0.54%

Traditional ROI: 0.12%

151 N Orlando Ave #115

Winter Park, FL

2 beds | 1 baths | 710 sq.ft.

$298,000

Airbnb cash on cash: 4.78%

Traditional cash on cash: 3.16%

Airbnb Rental Income: $3260

Traditional Rental Income: $2075

Airbnb ROI: 4.78%

Traditional ROI: 3.16%

2500 Lee Rd #222

Winter Park, FL

1 beds | 1 baths | 645 sq.ft.

$189,500

Airbnb cash on cash: 6.59%

Traditional cash on cash: 6.4%

Airbnb Rental Income: $2412

Traditional Rental Income: $1787

Airbnb ROI: 6.59%